Startseite Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
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Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone

  • Yong-Fu Qiu , Bin Lu , Yi-Yu Yan , Jin Zhou und Jin Wang EMAIL logo
Veröffentlicht/Copyright: 9. August 2019
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Green Processing and Synthesis
Aus der Zeitschrift Green Processing and Synthesis Band 8 Heft 1

Abstract

5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone 3, a key intermediate for preparing coenzyme Q compounds, was readily synthesized in two steps by a reaction sequence starting from the commercially available 3,4,5-trimethoxytoluene 1 via bromination and oxidation reactions. Persulfate salts were first employed as oxidants to synthesize 1,4-benzoquinone, the overall yield of title compound 3 was 65%.

Keywords: coenzyme Q; 1,4-benzoquinone; bromination; persulfate

1 Introduction

In synthetic chemistry, researchers are always seeking new methods for synthesising a specific compound that are important in many areas such as pharmaceutical industry. 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone (3) [1], is an important coenzyme Q compound [2], which facilitates electron-transfer activity [3] and radical properties in mitochondria [4]. In addition, compound 3 is also a key intermediate [5] in the preparation of other biologically active coenzyme Q analogues [6]. In 2000, Jung and co-workers [7] reported that coupling of compound 3 with isoprenylstannanes could efficiently produce coenzyme Q10 and its analogues, as shown in Scheme 1. CoQ10 is a lipid-soluble benzoquinone with a side-chain of 10 isoprenoid units (Scheme 1), acts as a free radical scavenging antioxidant [3]. CoQ10 has been widely used in the treatment of mitochondria disorders [8].

To date, methods for the synthesis of compound 3 are limited [9]. Most of the methods used CoQ0 as starting material, compound 3 was obtained by reaction with toxic bromine [10], and few syntheses leading to compound 3 have been disclosed [11]. Hence, based on our previous work on the synthesis of CoQ analogues [12, 13, 14, 15, 16], we now report an efficient synthetic path for compound 3 as shown in Scheme 2. The reaction is operationally simple and could be used in the preparation of other coenzyme Q analogues.

2 Experimental

All reactions were monitored by TLC (SiO2, petrol ether/ EtOAc 5:1). Melting points were measured on Melting Point M-565 (BuChi). NMR and mass spectra were recorded on a Bruker Avance III-HD 400 NMR and TripleTOF mass spectrometers, respectively. GC-Mass spectra were recorded on Triple Quadrupole GC/MS of Agilent 7890B-7000C. All reagents: e.g. NaBr, Na2S2O8, K2S2O8, (NH4)2S2O8 were purchased from Adamas, P. R. China, and used without further purification.

2.1 Synthetic procedure for 2-bromo-3,4, 5-trimethoxytoluene (2)

A mixture of 3,4,5-trimethoxytoluene 1 (0.72 g, 4 mmol) and NaBr (0.42 g, 4 mmol) were dissolved in acetic acid (4 mL). A solution of 30% H2O2 (2 mL, 18 mmol) was added dropwise at 40°C over a period of 1 h. The resulting mixture was quenched with water and extracted with petroleum ether. Combined the organic layers and evaporated in vacuo to afford a yellow oil 2 (1.04 g) in 100% yield. 1H NMR (400MHz, CDCl3): δ 6.61 (s, 1H, ArH), 3.89 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 2.37 (s, 3H, CH3). 13C NMR (101MHz, CDCl3): δ 152.2, 150.8, 141.1, 133.4, 110.8, 109.5, 61.1 (OCH3), 60.9 (OCH3), 56.1 (OCH3), 23.2 (CH3).

Scheme 1 Compound 3 and coenzyme Q10.
Scheme 1

Compound 3 and coenzyme Q10.

Scheme 2 Reagents and conditions: (a) NaBr, 30% H2O2, HOAc, 40°C, 1 h, 100%; (b) Sodium persulfate, HOAc/H2SO4, 80°C, 2 h, 65%.
Scheme 2

Reagents and conditions: (a) NaBr, 30% H2O2, HOAc, 40°C, 1 h, 100%; (b) Sodium persulfate, HOAc/H2SO4, 80°C, 2 h, 65%.

The data is consistent with the literature [13].

2.2 Synthesis of compound 3

Method (1): Compound 2 (0.44 g, 1.7 mmol) was dissolved in a mixture solvent of acetic acid (2.5 mL) and H2SO4 (0.25 mL), then a solution of Na2S2O8 (0.80 g, 3.4 mmol) in H2O (5 mL) was added dropwise over 5 min. The mixture was stirred and heated at 80°C for another 2 h and extracted with dichloromethane. Combined organic layers, and washed with H2O and NaHCO3, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by a flash column (PE/EtOAc 6:1) to give red solid 3 (0.28 g, 65% yield).

Method (2): A solution of K2S2O8 (3.4 mmol) in H2O (8 mL) was added dropwise to a mixture of compound 2 (0.44 g, 1.7 mmol) in acetic acid (2.5 mL) and H2SO4 (0.25 mL). The reaction mixture was heated at 80°C for 2 h, quenched with water and extracted with dichloromethane. The organic phases were washed with H2O and Brine, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue oil was purified by a flash column to give red solid 3 (0.26 g, 60% yield).

Method (3): To a mixture of Compound 2 (0.44 g, 1.7 mmol) in HOAc (2.5 mL) and H2SO4 (0.25 mL) was added dropwise by a solution of (NH4)2S 2O 8 (3.4 mmol) in H2O (6 mL) over 5 min. The reaction mixture was heated at 80°C for 2 h and extracted with dichloromethane. The combined organic phases were washed with H2O and NaHCO3, dried over Na2SO4, and evaporated in vacuo. The residue oil was purified by a flash column to give red solid 3 (0.17 g, 40% yield). m.p. 68 - 69°C (lit. 67-69°C [10]). 96% purity by HPLC. 1H NMR (400 MHz, CDCl3): δ 4.04 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 2.21 (s, 3H, CH3). 13C NMR (101MHz, CDCl3): δ 181.0 (C=O), 176.7 (C=O), 145.2, 144.1, 143.8, 133.6, 61.58 (OCH3), 61.33 (OCH3), 16.75 (CH3). GC-MS (EI): m/z = 260.

Table 1

Synthesis of compound 3 under different persulfate.

EntryOxidantTime (h)Temp (°C)Yield (%)
1Na2S2O828065
2K2S2O828060
3(NH4)2S2O828040

  1. Conditions: 2 (1.7 mmol), persulfate (3.4 mmol), HOAc-H2SO4 (v/v = 10:1).

The data is consistent with the literature [4].

3 Results and discussion

As shown in Scheme 2, treatment of 3,4,5-trimethoxytoluene (1) with NaBr and 30% in acetic acid at 40°C gave compound 2 in 100% yield. Finally, compound 2 was oxidized with a persulfate compound in HOAc-H2SO4 mixed solvent (v/v = 10:1) to afford compound 3 (Table 1). The reaction is conducted without using any metal catalyst. This environmentally friendly procedure is based on the persulfate oxidant as an oxygen atom donor, and the HOAc-H2SO4 solvent as proton atom in this transformation [2]. The use of (NH4)2S2O8 as oxidant in HOAc-H2SO4 (10:1) mixed solvent gave 3 in a yield of 40% (entry 3, Table 1). When utilized K2S2O8 as oxidant in the same mixed solvent HOAc-H2SO4 (10:1) can improve the reaction yield to 60% (entry 2, Table 1). The best yield was obtained using Na2S2O8 as oxidant in HOAc-H2SO4 (10:1) solvent system, which gave the desired compound 3 in 65% yield (entry 1, Table 1).

4 Conclusion

In summary, we developed a two-step synthetic protocol for the preparation of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone (3) from the cheap and readily available 3,4,5-trimethoxytoluene (1). The bromination reaction utilize NaBr–H2O2 system as a green brominating agent instead of bromine and NBS, the reaction is clean and easy work up without purification. Persulfate salts were first employed as oxidants to synthesize 1,4-benzoquinone under mild condisitons, the chemistry was clean and easy work up. This method is potentially applicable for the the synthesis of a wide variety of coenzyme Q compounds [14,15].

#Yong-Fu Qiu and Bin Lu These authors contributed equally to this work.

Acknowledgments

We thank the National Natural Science Foundation of China (Nos. 31600740 and 81803353), the Natural Science Foundation of Jiangsu Province (BK20160443), the Six Talent Peaks Project in Jiangsu Province (SWYY-094), the Jiangsu Provincial Key Laboratory for Bioresources of Saline Soils (Nos. JKLBS2016013 and JKLBS2017010) for financial support.

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Received: 2019-01-25
Accepted: 2019-06-02
Published Online: 2019-08-09
Published in Print: 2019-01-28

© 2019 Qiu et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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https://doi.org/10.1515/gps-2019-0052
Schlagwörter für diesen Artikel
coenzyme Q; 1,4-benzoquinone; bromination; persulfate
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  44. Use of deep eutectic solvents as catalyst: A mini-review
  45. Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol
  46. Green and eco-friendly synthesis of Co3O4 and Ag-Co3O4: Characterization and photo-catalytic activity
  47. Adsorption optimized of the coal-based material and application for cyanide wastewater treatment
  48. Aloe vera leaf extract mediated green synthesis of selenium nanoparticles and assessment of their In vitro antimicrobial activity against spoilage fungi and pathogenic bacteria strains
  49. Waste phenolic resin derived activated carbon by microwave-assisted KOH activation and application to dye wastewater treatment
  50. Direct ethanol production from cellulose by consortium of Trichoderma reesei and Candida molischiana
  51. Agricultural waste biomass-assisted nanostructures: Synthesis and application
  52. Biodiesel production from rubber seed oil using calcium oxide derived from eggshell as catalyst – optimization and modeling studies
  53. Study of fabrication of fully aqueous solution processed SnS quantum dot-sensitized solar cell
  54. Assessment of aqueous extract of Gypsophila aretioides for inhibitory effects on calcium carbonate formation
  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
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Heruntergeladen am 7.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/gps-2019-0052/html
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